Potassium Phosphate, Tribasic → HCID 24826506, compound

HRID 910973Notes

Reaction equation

HRID 910973 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:6]([C:11]2(C)CS[C:13](N)=[N:12]2)=NC=C[CH:10]=1.[CH3:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1.ClC1C=C(OC2C=CC=CC=2Cl)C=CN=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:13][N:12]=[C:11]([NH:28][C:25]2[S:26][CH:27]=[C:23]([CH3:22])[N:24]=2)[CH:6]=1

Participants

7

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 63777947HCID 63777947, compoundHCID 86634727HCID 86634727, compound

Product 1

HCID 24826506HCID 24826506, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Preparation of N-(4-(2-chloro-phenoxypyridin-2-yl)-4-methylthiazol-2-amine: Using the method of Example 3, Step B, 4-methylthiazol-2-amine (0.238 g, 2.08 mmol), 2-chloro-4-(2-chlorophenoxy)pyridine (0.500 g, 2.08 mmol), potassium phosphate (0.486 g, 2.29 mmol), Pd2(dba)3 (0.095 g, 0.104 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.060 g, 0.104 mmol) were reacted to provide N-(4-(2-chlorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine (0.293 g, 44% yield). 1H NMR (d6-DMSO) δ 11.00 (bs, 1H), 8.18 (d, 1H), 7.68 (d, 1H), 7.49 (t, 1H), 7.36-7.40 (m, 2H), 6.47-6.53 (m, 3H), 2.20 (s, 3H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5830c73b546844199395c199533e1d9a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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